Nitric Acid → 6-Nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid
Reaction equation
[NH:1]([C:5]1[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]([C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C(OC(=O)C)(=O)C.[N+:25]([O-:28])([OH:27])=[O:26]>C(O)(=O)C>[N+:25]([C:6]1[CH:7]=[C:8]([C:15]([OH:17])=[O:16])[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[C:5]=1[NH:1][C:2]([CH3:4])=[O:3])([O-:27])=[O:26].[N+:25]([C:7]1[CH:6]=[C:5]([NH:1][C:2]([CH3:4])=[O:3])[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]=1[C:15]([OH:17])=[O:16])([O-:28])=[O:26]Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
42 g of 8-acetamino-1,4-benzodioxane-5-carboxylic acid, 75 ml of acetic acid and 75 ml of acetic anhydride were introduced into a balloon flask and then a solution of 17.5 ml of nitric acid (d=1.49) in 17 ml of acetic acid was added, with the temperature being left rising. After dissolution and crystallization, 50 ml of acetic acid were added. The mixture was agitated at 40°-45° C. and then cooled to 20° C. The precipitate was dried off, washed with acetic acid and water and dried. 13.5 g of a 50% mixture of 7-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid and 6-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid were obtained. The 7-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid was separated and then treated according to the process of Example 31 with isobutyl chloroformate and diethylaminoethylamine. N-(diethylaminoethyl)-7-nitro-8-acetamino-1,4-benzodioxane-5-carboxamide was obtained. The structure was confirmed by nuclear magnetic resonance analysis.
Workup
- waitbeing left
- additionwere added
- customThe precipitate was dried off
- washwashed with acetic acid and water
- customdried
Sources & evidence
- ORD record
- ord-5e029a19e76b4cf99f3a2cdb701f6c4c
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255580
Reaction notes
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